Amphiphilic Spruce Galactoglucomannan Derivatives Based on Naturally-Occurring Fatty Acids

Daniel Dax, Patrik Eklund, Jarl Hemming, Jawad Sarfraz, Peter Backman, Chunlin Xu, Stefan Willför

Abstract


A class of nonionic polysaccharides-based surfactants were synthesised from O-acetyl galactoglucomannan (GGM), water-soluble hemicelluloses from spruce, using naturally-occurring saturated fatty acids, CH3(CH2)nCOOH (n = 7, 12, and 16). Hemicelluloses can be recovered from waste-streams of papermaking and agricultural processes or isolated by hot water extraction of plant tissues integrated into a biorefinery process. Fatty acids can be recovered as byproducts of the agricultural and food industries. Different synthesis routes were applied to yield amphiphilic derivatives with either a grafted or block structure. Fatty acids activated with 1,1′-carbonyldiimidazole (CDI) were grafted to the backbone of GGM molecules on their hydroxyl groups. Alternatively, synthesised amino-activated fatty acids using ethylenediamine were reacted with the reducing end of GGM. By adjusting the reagent ratios, GGM-based surfactants with different hydrophilic to hydrophobic ratios were prepared. Their surface activity was assessed by measuring the surface tension in water. This study presents an approach to design carbohydrate-based surfactants using naturally-occurring fatty acids that may find potential applications in such areas as food, cosmetic, and paint formulations.

Keywords


Amphiphilic; Fatty acid; Hemicelluloses; Galactoglucomannan; Reductive amination; Surfactant; Surface tension

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